


Cherryberry Kinktober 2019

by benguiat



Category: Undertale (Video Game)
Genre: Bondage, Breast Fucking, Breast Worship, Cherryberry - Freeform, Deepthroating, Dom/sub, Fluff, Gags, Intercrural Sex, Kinktober, Kinktober 2019, Lingerie, M/M, Nipple Piercings, Nipple Play, Orgasm Delay/Denial, Orgasm Denial, Overstimulation, Praise, Teasing, Titfucking, Underfell Sans (Undertale), Underswap Sans (Undertale), bratty sub, gagging
Language: English
Status: Completed
Published: 2019-10-01
Updated: 2019-10-04
Packaged: 2020-11-09 06:47:21
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 3,719
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20849228
Author URL: https://archiveofourown.org/users/benguiat/pseuds/benguiat
Summary: Some Cherryberry themed Kinktober prompts! Different versions and dynamics of the ship, but expect mostly Sub Red.DISCONTINUED, just some cherryberry smut oneshots now





	1. Lingerie, Deepthroating, Overstimulation

**Author's Note:**

> Thanks for reading this Cherryberry themed kinktober fic! I'll try to explore different dynamics between these two throughout the month, but tbh it'll probably be mostly sub bara!Red bc big subs is one of my fav kinks. I did minimal editing on this to get it out in time so apologies if there's any errors! I'll come back and edit it later.
> 
> I'll be using this list here: https://tomanonuniverse.tumblr.com/post/188003753247/my-own-kinktober-2019-list
> 
> Prompts: Deepthroating | Lingerie | Overstimulation
> 
> Warnings: (hinted) low self confidence?  
(we're starting out pretty fluffy here lads)

“YOU LOOK SO _ CUTE!” _

Doubtful. Red was a nearly 6-foot mass of chubby ecto and scarred, chipped bones. Some frilly painties weren’t going to change that.

Yes, the lingerie had been Red’s idea to start with, but it was a mistake letting Blue pick something out for him. _ Red _ had been thinking of something dark, sexy and seductive, something that’d leave his datemate slack-jawed and drooling. _ Blue _ had picked out a delicate, sheer babydoll accented with ribbons and lace, and tie-side panties in a pale shade of icy blue.

“wasn’t s’posed t’ be _ cute, _ ” Red grumbled, decidedly _ not _looking down at his datemate, who was probably all heart-eye’d and smug. He’d nearly refused to be seen in the stupid getup at all, having spent a good ten minutes glaring at his reflection in the bathroom before working up the nerve to come out. “this wasn’t what i was goin’ for…”

“OH, PLEASE DON’T TAKE IT OFF SO SOON!” Blue pleaded, and when Red finally spared him a look his eyes were indeed widely blown hearts, but there was no smugness to be found. Only gleeful adoration. “I mean... if you’re really that uncomfortable, I understand, and I won’t force you to keep it on. But you look so lovely, Red!”

The Fell monster felt his face growing hot, and turned away again to hide the blush spreading across his face, scoffing. “i ain’t ‘_ cute’ _ or ‘ _ lovely’ _ . i’m gross, an’ I look like a fuckin’ _ clown _ in this, tryin’ t’be anything else-”

“HEY!! THAT’S MY DATEMATE YOU’RE TALKING ABOUT!” Blue snapped, demeanor suddenly firm and no-nonsense, though the heart eyes still remained. He grabbed Red’s much larger, clawed hand without hesitation and pulled his much taller datemate down to eye-level. “WHAT HAVE WE SAID ABOUT THAT SELF-DEPRECATING LANGUAGE?”

“ugh, _ blue _,” Red tried to pull away, but Blue was strong for such a small guy, and his grip held steady. “it’s nothin’, ya don’t gotta do this shit…” He tried to shy away from his datemate’s intense gaze, but Blue took his chin in hand and gently guided his head back.

“Nope!” the Tale monster chirped, popping the ‘P’ before breaking his serious facade and smiling toothily. “It’s personal now! You’ve forced my hand! I have no choice but to show you how beautiful you are!” In one swift move, Blue shifted and lifted Red into his arms.

Lovestruck and going stupid in the process, Red couldn’t react more than a pathetic whimper as his tiny datemate nearly half his size swept him off his feet into a pseudo bridal carry. He was gently deposited on their shared bed, and was immediately attacked on all sides by chaste kisses against his skull, nasal bone, and cheekbones. Red snorted as Blue peppered ticklish smooches all over his face, eventually pulling him down to press their mouths together. When Red tried to add some tongue into the mix Blue slipped away in favor of leaving a trail of kisses down Red’s neck.

“heh, that fuckin’ tickles, q-quit it!” Red sniggered, laughter abruptly cutting off with a gasp as Blue moved lower to the beasts he’d summoned to fill out the lingerie. Sliding the fabric away, Blue took one mound in each hand, unable to fully cup them due to their size difference. He’d always found it hot, and always made a point of saying so.

“You at least have to admit that _ these _ are lovely, Red,” Blue hummed, kneading them gently. “Hehehe, I could play with these for _ hours.” _

Red tried to roll his eyes and look unimpressed… but Blue was always fucking amazing with his hands. “hah, y-ya just… y’just like b-big tits.”

“I’m not ashamed to admit it!” Red was helpless to keep in a yelp as Blue roughly flicked his nipples. _ There was that smug fucking face. _ “As much as I _ would _ love to stay like this for hours, maybe another night.” Blue reached behind himself, and Red moaned as his cock was stroked through his panties. “That’s not what I’m after tonight.”

As always, Blue was skilled with his hands, and Red was fully hard in under a minute, straining against those stupid panties. He reached down to untie them, but his hand was pushed away, and he whined desperately. He knew he sounded fucking stupid, but _ fuck _, Blue drove him crazy.

“Be patient!” his tiny datemate scolded, leaning down to grab the ribbons at the sides of the panties, but only held them loosely. “Hehehe, you look like a perfect little present for me, all wrapped up in a bow!”

“blue, _ please,” _ Red groaned, throwing an arm over his face to hide how red his face probably was. “i’m beggin’ ya, blue, please, just fuck me already…”

“You’re so cute,” Blue cooed, ignoring his datemate’s pleas. He pressed a light, teasing kiss against the head of Red’s cock through the fabric, making him jump. “You look so lovely. I want to see your cute face, please? Let me see your lovely face and maybe I’ll give you what you want.” 

Red begrudgingly lifted his head. If he’d had a stomach, seeing the complete and unadulterated love on Blue’s face would have made him feel butterflies. As it were, he just felt weak- he just _ needed _ his datemate. “p-please, blue.”

Blue pulled the ties loose, and Red’s cock sprang to attention. Blue tossed the panties aside and licked a long stripe up the underside of it, and Red threw his head back in a groan. He choked as Blue squeezed the base of it, demanding his attention. “Eyes on me. I said I wanted to see all the cute faces you make.”

Red complied, but was barely able to keep it up as Blue slowly, inch by inch, started working himself down his datemate’s cock. The head pushed back against his throat, and Red groaned as it was swallowed down hungrily. He was always worried about his much smaller lover when they did this, urging him to take his time, to only take as much as he comfortably could, but as always Blue was determined, and didn’t pause until his face was flush against Red’s hips.

Blue’s reprieve only lasted a moment before he was slowly pulling back and pushing down again, further and further each time until he was able to start speeding up. Once he’d gotten into a rhythm he finally turned his intense gaze back onto Red, eyes fuzzy hearts, tears running down his face. It was overwhelming. Red tried several times to look away, but each time was swiftly reminded of where to keep his eyes with a dangerous brush of teeth against his sensitive shaft.

Somehow, even when he was gagging on Red’s cock, Blue could manage to look smug.

It wasn’t long before Red was cumming down his datemate’s throat, shuddering as Blue sucked down every last drop. Red waited for Blue to start easing off his cock, already planning on returning the favor. But instead of pulling off, sucked hard on his already softening cock.

“_ hahh _ , _ fuck- _ b-blue, i j-just came-” Red choked, moving to scoot backwards, but Blue followed him. “blue, please, s- _ sensitive- _fuck!” He pushed on Blue’s skull, who finally relented and let himself be guided back.

But not before wrapping a firm hand around Red’s cock and pumping roughly.

“We’re not done until I get you to admit it how lovely you are,” Blue tried to coo, voice raspy from his previous work. He continued pumping, unheeding of Red’s pleas, even as overstimulated tears pricked at his eye sockets.

Blue still had that smug fucking look on his face.

“And then we’ll keep going until _ I _ think you’re fully convinced.”


	2. Intercrural Sex, Gagging

**Notes for the Chapter:**

> Two for two!! Hopefully I can keep this streak going. Chapter 2 features some more bara!Red ;)
> 
> Prompts: Intercrural sex | Gagging
> 
> Warnings/Additional tags: Bratty sub, Bondage, Orgasm denial  
(all consensual)

Sometimes Red could really be a brat.

Blue was understanding about his reasonings, of course! Red didn't have much experience with intimacy, and _ certainly _ not with letting someone else taking charge. Sometimes during their sessions he got a little intimidated, and this manifested itself in the form of a _ lot _ of snark and lashing out. And while Blue _ did _ understand where the behavior was coming from, that didn’t mean it was acceptable. Not at all!

Red sure was lucky to have a datemate willing to teach him to correct such behavior!

“shit, c’mon already,” Red huffed, shifting in frustration as much as he could in his current position. Face down on the bed and legs hanging off the edge, wrist loosely tied behind his back (only enough so that he could slip out if he really wanted to) and knees cinched tightly, pressing his thighs together. “just stick it in, would ya!”

Blue ignored the demand and continued thrusting himself between his datemate’s thighs, as he had been for the past 20 minutes. He’d generously let his cock rub against Red’s pussy more often than he ignored it, enough to work Red up not nearly enough to let him cum. Blue have been taking his time so far; Red’s soft ecto felt amazing around him, wet, sticky juices from his own cunt lubricating them. It was hardly the cruelest punishment Blue had ever come up with, and frankly he thought Red was overreacting!

“Oh, you don’t want that,” Blue scoffed, voice dripping with sarcasm to match the snarky tone Red had been taking with him all night. “What was it you said? Something about how tiny I am?” He let the head of his cock catch against Red’s clit, reveling in his datemate’s surprised moan before pulling away and leaving Red whining for more. “Something along the lines of my dick being so small I shouldn’t even bother? Don’t worry; I won’t!”

“fine, i’m sorry your dick is the size of a crayon,” Red spat, no remorse to be seen as he turned his head as much as he was able, just to be able to look Blue in the eye as he scowled. “now hurry up and fuck me.”

“Oh wow, what a lovely apology!” Blue jeered. “Why don’t you try again, and try to sound even _ less _ sincere, and we’ll see where that gets you?”

As expected, Red growled and instead shoved his face into a pillow to muffle his furious cursing. Blue paused his thrusts and waited patiently for the temper tantrum to taper off into disgruntled mumbles, and eventually silence. “Are you done yet? Ready to try again?” His answer was mumbled into the pillow. “I can’t hear you!”

Begrudgingly, Red lifted his head, turning upwards to give a much less potent glare. “m’sorry.”

“And _ what _ are you sorry for?”

“m’sorry for callin’ yer dick tiny,” Red ground out through gritted teeth. “please. fuck. me.”

“It still leaves something to be desired, but I’ll forgive you this time!” Blue relented, smiling sweetly. “Now, if you really want my cock so badly, why don’t you beg for it?”

“wha- fuck no, ya told me t’appologize and i did it!”

“Very poorly! Come on, all you have to do is ask _ nicely _.”

“fuck you.”

“All you have to say is ‘please may I have your cock in me’! I’ll even accept a simple ‘please, I’m begging’!”

“ya don't got nothin' worth beggin’ for!”

Alright! Red was _ really _ trying Blue’s patience today! And Blue had had about all he could take! He took a deep, calming breath before speaking in a soft, even tone. “Fine. I gave you a chance to apologize properly- multiple, even! So now you’re just going to have to sit there and take the rest of your punishment until _ I _ think you’ve learned your lesson.”

“ya _ asshole!” _ Red screeched indignantly, his struggling renewed with a furious passion. “i fuckin’ hate ya and yer stupid, smug-ass fuckin’ face-”

“As much as I love the sound of your voice, I’m getting tired of your whining. Keep it up and I might have to shut you up myself! Do you really want me to gag you?”

“heh, that’s _ laughable- _ yer short-ass arms can’t even reach as far up as my- _ ughk!” _ Red choked on his words- and his own underwear- when Blue used his magic to pick up the discarded clothing and shove it into Red’s open mouth, cramming it behind his teeth.

“There! Much better!” Blue said, falling out of the scene for a moment to rub his datemate’s bound wrists, prompting him to use their chosen hand signals. “Hey. Is this okay?”

Blue saw Red begin blushing furiously a moment before shoving his face back into the pillow, suddenly shy now that the scene had been momentarily paused. Groaning in embarrassment, only barely audible through the gag and the pillow, he snapped his fingers twice and gave a thumbs up, their signal to keep going.

“Good,” Blue encouraged, reaching around to reward Red with a few teasing circles around his clit, making his datemate moan and lean desperately into the touch. “Once I think you’ve learned your lesson I promise I’ll give you a nice reward. Ready to take the rest of your punishment?”

Red choked out a few garbled groans that sounded faintly like another “fuck you”. Blue sighed tiredly, flicking Red’s clit before withdrawing his hand completely, ignoring the furious grumbling that ensued as he resumed a fast, rough pace fucking this datemate’s deliciously slick thighs.

“Stars, you’re such a brat.”


	3. Breast Worship

**Summary for the Chapter:**

> posting day three on oct 4th.... forgive me ;-;
> 
> This chapter is a little longer than the others, maybe because I had no idea where I was going with this. But the result is breast worship with a little praise, teasing, nipple piercings and nipple play, and Red being a little more dom! (still a bottom tho.) I'm hoping I'll be able to post day 4's chapter later tonight. Rest assured, even if chapters are late, I WILL be finishing all 31 days.
> 
> Prompt: Breast Play  
Warnings/Additional tags: teasing, nipple piercings, nipple play, titfukcing, praise, unrealistic sex

Some people were ass guys. Some were boob guys. Some were thigh lovers, and leg guys. Blue was a self-proclaimed "all-of-the-above" guy, and loved to lavish attention on _ all _of his datemate.

Red didn't doubt that Blue loved all of him equally, but it was also easy to notice when and where his datemate’s eyes would linger. Particularly, on his rack. It wasn’t often that he summoned his tits, and that alone probably made them especially tantalizing, but they were pretty damn impressive, if he did say so. Pierced nipples, probably F or G sized, not that he had them out often enough for them to be worth measuring. (And yet, when he was gifted various lingerie to try on, Blue always managed to guess his size exactly right?)

He’d been teasing Blue for the few days, summoning his tits only to casually recline on the couch and lean heavily against his datemate, as per their evening routine. Blue’s attention would immediately shift away from the TV and towards the soft ecto pressing against him, brows waggling suggestively. “HELLO, WHAT’S ALL THIS FOR~?”

Red would return the look indifferently, replying with blunt innocence. “what’s what for.”

Blue would pause expectantly, like he was waiting for Red to continue, or crack a lewd joke, or flirt. When nothing came, he’d falter and avert his gaze, flushed with embarrassment. “O-OH, YOU WERE SERIOUS! I-I’M SORRY, I-I THOUGHT- NEVERMIND!”

Red struggled to hold in his laughter every time Blue would awkwardly backpedal. Blue wouldn’t make any more remarks or advances for the rest of the night, but every time Red glance over he caught his datemate ogling his chest from the corner of his eye. He repeated this kind of teasing several times over the next few days, with similar results. Blue was quick to stop asking about it, appearing to make an attempt at patiently waiting for Red to initiate anything (which didn’t happen). He was frequently caught staring.

It culminated into Blue coming home late one night after covering a shift for one of the Dogi. He trudged through the front door looking tense, not even bothering to kick the snow off his boots before toeing them off and leaving them in a pile at the door. Red decided to take pity, and instead of his plans for the night bent down for a hug.

“MMF!” Blue grunted in surprise as he was pulled forward, face suddenly sandwiched between Red’s tits. He was blushing in record time. “H-HI.”

It wasn’t often Blue got so flustered, but on the occasions it did happen, Red relished it. “hey, babe. long night?”

“I-IT WASN’T SO BAD,” Blue said loudly, even for him. He glanced at the breasts pillowing his skull before quickly tearing his eyes away, looking like he was struggling to control himself. “H-HOW WAS YOUR NIGHT?”

Red reached up to cup his tits and squish them against Blue’s cheeks, which quickly darkened until they were a royal blue. He made no effort to muffle his snickering. “aw, i was workin’ all night on yer surprise. ya don’t like’em?”

Blue sputtered incredulously. “WHAT- SURPRISE? Y-YOU’VE BEEN FLAUNTING THESE FOR DAYS AND HAVEN’T LET ME TOUCH THEM!”

“ya don’t want’em?”

“WH- I DO, BUT-”

“fine,” Red shrugged nonchalantly, withdrawing from his datemate completely. “no skin off my nose.”

“YOU HAVE NEITHER SKIN, NOR A- what is that.”

Red smirked; Blue had finally gotten a good look at his old, threadbare top. The raised nubs of his nipples and distinct heart shapes were pronounced against the thin fabric. “yer surprise. not gonna let it go to waste, are ya? come’n get it.”

Like a man possessed, Blue eagerly obeyed and pushed the ratty old tank top up and out of the way. He froze up again at the reveal of the delicate little heart-shaped rings framing Red’s nipples, mesmerized by the sight.

So mesmerized, apparently, that he couldn’t react. Red cleared his throat awkwardly, growing uncertain at his Blue’s unresponsiveness. “uh. d’ya... like’em? it’s okay if ya don’t, ya can tell me-”

“I LOVE THEM,” Blue exclaimed, pupils shifting to fuzzy little hearts of his own. His gaze was unwavering, asking breathlessly, “They’re so pretty… Can I touch? Please?”

Red grabbed Blue’s wrists and guided them up, where his datemate began thumbing his nipples and gently kneading the soft ecto. He chuckled through a groan, somehow both relaxing and tensing up under the attention. “that’s a stupid fuckin’ question. it’s _ yer _ suprise, dumbass.”

“How long have you been hiding these from me?”

“‘bout a week.”

“THAT LONG??”

“heh, well, i wanted t’ suprise ya, wanted there t’ be some buildup.”

“OH MY GOD, YOU _ HAVE _ BEEN TEASING ME ALL WEEK!! I _ KNEW _ YOU WERE JUST PLAY DUMB! YOU’VE GOT A LOT TO MAKE UP FOR MISTER!”

“well,” Red pulled them both through a shortcut leading into their room, tossing his tanktop onto the floor and flopping backwards onto their shared bed. “good thing we got all night, huh?”

Blue quickly shed his own clothing (placing them neatly in the hamper instead of just tossing them aside) before joining, straddling Red’s belly and hands hovering over the new piercings. “Can I touch?"

“blue, use’m as fuckin’ stress balls, i don’t care. go at it.”

“Red, that’s gross.” And yet, Blue hardly looked or sounded grossed out, eagerly groping and kneading one breast while fingering the piercing of the other. “I _ really _do like them… they’re so pretty…”

“i can tell,” Red sniggered, reaching down to play with the fuzzy magic at Blue’s pelvis, coaxing it to coalesce into a cock, what it lacked in length it made up for in width. Red smeared the pre gathering at the tip onto his fingers, giving it a few good strokes. “i’ve been catchin’ ya staring all week. pretty lewd of ya, huh?”

“W-Well you’ve been _ teasing _ me all week,” Blue grunted, thrusting into Red’s hand. He retaliated by gently flicking the lovely little hearts, smirking at the resulting groan. “Wouldn’t you say that _ that’s _ pretty l-lewd of _ you? _ Not to mention pretty cruel?”

“lemme make it up t’ ya, then,” Red grabbed his datemate’s hips and pulled them forward until the cock rest against Red’s sternum. He shoved Blue’s hands away to cup his breasts together, squeezing them around Blue’s cock. “why don’t ya go ahead and fuck my tits?”

“F-Fuck.” Needing no more convincing than that, Blue went right at it. His own abundant pre lubed the way, slicking up Red’s ecto. He immediately set an enthusiastic pace, no rhythm to his sloppy, jerky thrusting. It was rare for Red to see him so excited and flustered, a far cry from how composed and confident he usually was.

“ya look really good like this, babe,” Red hummed, letting his claws lightly scrape against the head of his datemate’s cock when it peaked out from between his own ecto. “when ya get all shy lookin’, like ya don’t know what t’ do with yerself. maybe i oughta tease ya more often?”

“_ Nooo! _ ” Blue whined, suddenly groping Red’s breasts and slotting the piercings between his fingers, roughly fondling them like he was worried Red was somehow about to take them away. “They’re so pretty- I love these, I love them, you need to let me play with them _ more! _ F-Fuck, I’m going to come-” He paused, looking like he was struggling to restrain himself. “Please, Red, I-I want to c-cum on your b-breasts.”

Red choked. “f-fuck, then d-do it.”

“Thank you!” Blue whined even as he pulled himself away, frantically stoking himself over mumblbing a stream of praises as if he were praying to some god. "Thank you, you're so perfect, I love you, you're so pretty and soft, thank you, I love you so much - _ fuck!" _

Ribbons of magic splattered against Red's breasts, painting them in a contrast of blue against his own ecto. Blue looked infinitely more tired now than he had when he'd walked through the front door, but now with a satisfied, relaxed slump to his shoulders. Red gently pulled his datemate down to lay beside him, tucking Blue under his arm and close to his side, much to Blue's chargin.

"Noo," he protested without much energy behind it. "You're all messy now, you need to clean up before bed…"

"don't worry about it," Red said dismissively, gathering up some of the mess onto his fingers and laving his tongue over them sloppily. "i got it covered, babe."

As expected, Blue was eyeing him with interest, and leaned over. "Let me help." He began lapping up his own spilled magic, working dutifully to make sure no stickiness remained. He finished the job with a hard suck and a moan around Red’s nipple.

Red yelped in surprise playfully smacked the back of Blue’s skull. “little shit.”

Blue chuckled and left a soft kiss as an apology. “They’re so pretty. You should wear them more often.”

“heh. maybe when i think ya earned ’em.”

“Oh no, you’re so mean, heheheh... Thank you. I love you.”

“love ya too.”


End file.
